


What you do when you lose a bet

by thingsiwontadmittohavewritten



Category: Teen Wolf (TV)
Genre: (it's not either), (it's not though), Anonymous Sex, Cross dressing - freeform, Embarrassment, Freeform, M/M, Not that much porn though, Orgasm Delay/Denial, Plot What Plot/Porn Without Plot, Possible non-con, Possibly cheating - freeform, but otherwise AU, werewolf Derek (implied)
Language: English
Status: Completed
Published: 2016-06-26
Updated: 2016-06-26
Packaged: 2018-07-18 11:14:04
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,742
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7312786
Author URL: https://archiveofourown.org/users/thingsiwontadmittohavewritten/pseuds/thingsiwontadmittohavewritten
Summary: <blockquote class="userstuff">
              <p>Wherein Stiles lost a bet and is dragged to a concert wearing a dress, and then somehow ends up getting fucked</p>
            </blockquote>





	What you do when you lose a bet

**Author's Note:**

> Usual disclaimers
> 
> Kudos and comments welcome, let me know if I forgot to tag something important
> 
> End notes contain fic spoilers
> 
> Edit: I was told to move the rating.

Most of the time Stiles likes his friends, today is not most of the time though and as of right now he can’t help but actually loathe every single last one of them though he hates Lydia with a passion he has never experienced before.  
That it’s all his own fault doesn’t really make it any better, he should’ve known better than making a bet with Lydia and he should definitely have known better than letting her win the right to decide everything for him for an entire day. He should have, he didn’t and now here he is, hating Lydia with his entire being.  
And it had all started so well, it had looked as if he was winning and then they served mystery meat on a pizza day. Stiles was mortified, not only had he lost a bet that should’ve been impossible to lose (the cafeteria had not changed their meal rotation _once_ in the last three years) but neither did he get pizza. It wasn’t until later he realized that everything could get much worse.  
  


Saturday morning at 8 saw Lydia standing in his bedroom pouring a glass of water over his head. By the time Stiles was somewhat coherent and dressed she then proceeded to drag him out the house, into her car and drove off. Then he was herded inside a beauty parlor where squabbling women proceeded to strip him and smear warm wax over him and removing every offensive hair they saw. Stiles never really understood why women willingly would subjugate themselves to this kind of treatment regularly, but most of his sympathy was gone by the time they tore off his sparse chest hair and was replaced by murderous thoughts by the time Miguel (he will admit that it’s funny when his hair has grown back) was waxing his groin, the only thing keeping him from voicing any of them was the real threat of Lydia telling him to suck it up or she’d do it. There was no way he would _ever_ let Lydia Martin near his junk with hot wax, or without for that matter.  
After the torture of hair removal he was then treated to things much more to his liking, especially the massage had him almost forgetting the creative ways he could kill Lydia and his other friends, and by the time they drove back to Lydia’s place he had even forgiven her for the brutal wakeup call at ass o’clock on a Saturday.  
The rest of the day was spent doing homework and talking even playing a few games even if Lydia wasn’t all that into those. He even found himself getting excited when she pulled out a couple of tickets to a concert he hadn’t heard of telling him they were going. Of course she ruined it by taking out a suit bag from her closet and telling him that was what he was wearing. He looked at the garments in horror his eyes pleading for her to tell him it was a joke, of course she didn’t expect him to wear _that_ but she simply rose her perfect eyebrow at him, turned and threw something on the bed beside the bag and left the room with a last: **”You lost, Stilinski, man up.”**  
Defeated he brought everything along and once the bathroom door was securely locked behind him he stripped. Looking at the pile of items Lydia wanted him to wear he felt heat rising in his cheeks, but knowing she’d skin him alive if he didn’t do as she wanted he poured lube on his fingers and carefully started stretching himself before inserting the black plug, quickly followed by a thong, garter belt, stockings and the short dress. The bodice is corset like and tight enough to be a little constricting while the skirt is layered and billows around his legs. It’s short enough that Stiles can feel the air against his bare ass cheeks, but long enough that he’s certain nobody will be able to tell what he’s wearing underneath.  
He’s long done by the time Lydia comes back, eyeing him critically before nodding and declaring them ready to go.

Waiting outside in line is uncomfortable with basically every other person staring at him as if he’s a piece of gum under their shoes. The attention makes him go stiff and even clumsier than he usually is, but Lydia simply drags him along to the end of the line where they’re let in with nothing but a nod from the bouncer. Once inside in the dark Stiles lets go of a breath he didn’t realize he was holding and then he’s led by Lydia to the wall opposite of where they are.  
Out from the scrutiny of strangers he begins to relax and soon he’s just one body among many others and nobody cares what he looks like and he relaxes in the anonymity and the reassuring squeeze of Lydia’s hand against his own. Then the band finally starts playing and it’s a thousand times better than Stiles could imagine, not music he’d normally listen to himself, but he can’t help the feeling of being swept away by the band anyway. The music is hard and heavy, the bass thrumming through his gut and the lead singer’s voice is frail and forceful, screaming every emotion with an intensity that makes him want to weep or hug her tight, telling her everything will be all right.  
The sea of people around him move and he moves along with it, people bumping into him left and right and back but so does he, and he pays it no mind, until a hand clamp down on his neck and another pulling him by the hip flush against the hard, rigid lines of a man, warm breath panted out against his ear as an erection is slowly grinded up against his almost bare ass, and he wants to move his head but he can’t with the hand against his neck, and then Lydia is next to him, telling him to look at the stage because that’s where the excitement is, and she’s gone in the move of the masses and so is the hand, gone to lift the skirt he’s wearing exposing his heated flesh to the air, and then that warm, large hand is kneading his cheek, hiding it even as its exposed and the movement jostles the plug, the end catching on the thong pulling a strangled sound from him. The man behind him responds by pressing his – no longer jeans clad – cock against Stiles’ ass, and he can feel it leave traces of precome on his skin, before the man gently pulls the thong aside, removes the plug and then Stiles is so full he almost sobs with it, the man behind him thrusting with the sea of people, fucking Stiles in their rhythm his hands a warm solid weight on Stiles hips, keeping him grounded and keeping up the illusion that nothing untoward is going on.  
The man’s movements are slow but calculated designed to bring himself pleasure but at the same time giving Stiles as little as possible. When the man hits Stiles’ prostate – once every five or so thrust – the shock makes him pant and moan, his cock twitching in its confinements and Stiles _wants_ so bad, but the man’s growls in his ear and the feel of teeth against his lobe tells him that he’ll have to settle with what he’s given.  
Finally when the music reaches it crescendo so does the man, as he goes stiff behind him and Stiles can feel the man emptying himself inside Stiles’ willing body. When he withdraws he replaces his cock with the plug, trapping his release inside even as he thrusts it in and out a few times before letting go, putting the thong back in place and then wipes the remnants of seed and lube of against Stiles skin and the fabric in his ass.  
Walking with Lydia back to her car is torture and he keeps throwing suspicious look to her. The girl doesn’t say anything out of the ordinary, exclaiming about how great this evening was and how glad she is he came along. She drives him home calling him a good sport and then slaps his ass as he leaves the car. He scowls after her until he can’t see her taillight before letting himself inside, slowly walking up the stairs. The plug moves with him and he thinks he can hear the squelch of lube and semen inside him and it has his face burning in embarrassment when he thinks about what happened less than an hour ago, but even then he can’t help but being helplessly turned on by it and he decides to forego the shower and go straight to bed.  
What he hadn’t planned on was to be gripped by strong hands with sharp claws that rips his clothes away from his body, nearly tearing the prison around his cock into a thousand pieces, and then Stiles is on the bed his upper body pressed into the mattress and his ass high in the air, his legs spread to expose him and then there’s a tongue on him, long and moist and warm licking all over the skin between his cheeks over the jeweled end of the plug before it’s tugged out of him for the second time tonight and he can feel it leaking out of him, but before he can speak he’s breached again and this time there’s nothing slow about it as the one behind him simply bottoms out in a practiced move, forcing his considerable girth and length inside Stiles’ body, not giving him a second to adjust but demands him to take. There are bruising hands on his hips and the speed is relentless as his prostate is hit dead on with every thrust. Stiles’ mouth is open on a wordless scream, his eyes closed and as his ass is flooded once more his own cock twists and starts spurting, his walls clenching down on the hardness inside him before he’s suddenly empty again, as the man behind him paints his skin with the last of his release.  
Stiles simply collapses without a sound and is almost half asleep when his boyfriend lays down beside him, molding him against his sculpted chest whispering words of love and adoration in the boy’s ear.

**Author's Note:**

> In case you wondered: Lydia didn't pick out the things Stiles is wearing, but wether it's him or Derek who did I'm not entirely sure. And just to clarify, Stiles only have sex with Derek, and therefor no actual cheating or non-con


End file.
